WO2005007946A1 - Matiere a mouler ou a filer thermostable - Google Patents

Matiere a mouler ou a filer thermostable Download PDF

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Publication number
WO2005007946A1
WO2005007946A1 PCT/DE2004/001235 DE2004001235W WO2005007946A1 WO 2005007946 A1 WO2005007946 A1 WO 2005007946A1 DE 2004001235 W DE2004001235 W DE 2004001235W WO 2005007946 A1 WO2005007946 A1 WO 2005007946A1
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WO
WIPO (PCT)
Prior art keywords
spinning
molding
stabilizers
bound
mass
Prior art date
Application number
PCT/DE2004/001235
Other languages
German (de)
English (en)
Inventor
Reiner BÜTTNER
Frank Wendler
Gerhard Graness
Frank Meister
Waldemar Dohrn
Original Assignee
Thüringisches Institut für Textil- und Kunststoff-Forschung e.V.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Thüringisches Institut für Textil- und Kunststoff-Forschung e.V. filed Critical Thüringisches Institut für Textil- und Kunststoff-Forschung e.V.
Priority to AT0923604A priority Critical patent/AT504005B1/de
Priority to GB0600707A priority patent/GB2419885C/en
Publication of WO2005007946A1 publication Critical patent/WO2005007946A1/fr

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Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/10—Other agents for modifying properties
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof

Definitions

  • the invention relates to a process for the production of thermally stable molding or spinning solutions, the cellulose, an aqueous stable tertiary amine oxide, preferably N-methylmorpholine-N-oxide (NMMO), a non-solvent for cellulose, in particular water, stabilizers and optionally contain different additives to modify the properties, and which are spun into cellulosic fibers or warped into films using the dry-wet extrusion process.
  • NMMO N-methylmorpholine-N-oxide
  • Tertiary amine oxides are known as solvents from US Pat. No. 2,179,181. These amine oxides are not very stable thermally. So builds z. B. N-methylmorpholine-N-oxide to N-methylmorpholine, morpholine, N-formylmorpholine, formaldehyde and C0 2 . Stability can NEN by Schwermetallio- ', such as iron and copper be further reduced (Ferris et al, J. Org. Chem., 33, page 3493 (1968), Taeger et al, formulas, fibrous materials, finished goods, 4, pages 14-22 (1985)). However, metal ions cannot be excluded due to the raw materials used and the system design.
  • DD 158656 describes a process for reducing cellulose degradation in cellulose solutions containing inoxide. Substances are added to the solution or the amine oxide which have a reducing effect on amine oxides. Such substances include amines, urea, hydroxylamine, hydrazine, sulfites, thiosulfates, dithionites, thiourea, sulfur, aldehydes and reducing sugars.
  • DE 3034685 adds organic compounds which have at least four carbon atoms, at least two conjugated double bonds and at least two hydroxyl and / or amino groups with at least one unsubstituted hydrogen atom and / or contain glyceryl aldehyde.
  • DE 3034685 mentions propyl ester of gallic acid as the most effective stabilizer. According to DD-A-0218104, this process has disadvantages because the cellulose solution is discolored or reaction products of the additives mentioned accumulate when the amine oxide is circulated. In addition, the additives cannot effectively prevent the additional cellulose degradation catalyzed by iron compounds and other impurities.
  • solutions of cellulose in N-methylmorpholine-N-oxide can be stabilized against thermooxidative degradation by using substituted phenols, preferably 2,6-di-ter. -butyl-p-cresol.
  • substituted phenols preferably 2,6-di-ter. -butyl-p-cresol.
  • the stabilizing effect does not lead to sufficient stability of the spinning solution.
  • Methylmorpholine-N-oxide can be thermally stabilized by adding phosphoric acid and phosphonic acid or their salts. According to DD-A-0229708, the stabilizing effect is not sufficient.
  • thermally stable cellulose-amine oxide solutions can be obtained if one or more basic substances are added to the amine oxide in amounts between 0.1 and 10% by mass, based on the cellulose solution.
  • alkali hydroxides e.g. B. caustic soda
  • basic salts e.g. B. Na 2 C0 3
  • organic nitrogen bases recommended.
  • WO 95/23827 states that increased thermal stability of the spinning solution is achieved if an aqueous amine oxide solution adjusted to pH 10.5-13.5 with sodium hydroxide solution is used to dissolve the cellulose.
  • EP 0670917 B1 states that the addition of basic substances cannot prevent the cellulose from being broken down under prolonged thermal stress.
  • EP 0670917 B1 proposes to stabilize the spinning solution by adding one or more stabilizers to the spinning solution which have an overall antioxidative effect on the cellulose and are sufficiently basic.
  • the solutions proposed in the cited patents for stabilizing the spinning solutions relate exclusively to spinning solutions which do not contain any additional additives for modifying the shaped bodies. In many cases, the addition of additives leads to a further instability of the spinning solution, which increases the existing risk of exothermic reaction of the spinning solution.
  • Experiments with weakly acidic ion exchangers modified spinning solutions, which were stabilized according to the prior art with gallic acid propyl ester and sodium hydroxide solution showed a reduced onset temperature and led to an exothermic reaction during extrusion.
  • Spinning solutions modified with activated carbon showed a similar result.
  • the viscosity of the spinning solution drops due to the breakdown of the Cellulose heavily.
  • a spinning of these solutions is not possible according to the known state of stabilization.
  • the aim of the invention is to develop a process for the production of thermally stable additives-modified cellulose amine oxide solutions which makes it possible to suppress the risk of exothermic occurrence of the molding or spinning solution, to spin regenerated cellulose molded articles with a sufficiently high degree of polymerization and to Keep degradation of the amine oxide low.
  • the aim of the invention is achieved in that a molding or spinning solution which contains cellulose, an aqueous tertiary amine oxide, a non-solvent for cellulose and optionally additives for property modification in a sufficient basic setting, with one or more polymer-bound stabilizers binding properties for metal ions alone and / or aldehyde-binding properties in amounts of at least 0.01% by mass based on the cellulose solution.
  • a molding or spinning solution which contains cellulose, an aqueous tertiary amine oxide, a non-solvent for cellulose and optionally additives for property modification in a sufficient basic setting, with one or more polymer-bound stabilizers binding properties for metal ions alone and / or aldehyde-binding properties in amounts of at least 0.01% by mass based on the cellulose solution.
  • stabilizers can be used alone or in a mixture with other complexing agents and basic substances.
  • the invention is based on the finding that by binding metal ions such as Fe 2+ , Fe 3+ and Cu + , Cu 2+ and the binding of formaldehyde, the degradation of the NMMO and the cellulose can be significantly reduced and thus the risk of an exothermic reaction , These substances are preferably added during the preparation of the molding or spinning solution.
  • polymer-bound stabilizers for the selective binding of metallo NEN are the alkali metal salts of weakly acidic chelate-forming imino-diacetic acid bound to styrene-divinylbenzene copolymer or polymer-bound carboxyl groups or their alkali metal salts, such as.
  • a styrene-divinylbenzene copolymer-bonded benzylamine is used to bind aldehydes, especially formaldehyde.
  • the mash-modified molding or spinning solution is preferably adjusted to a pH between 11-12. If molding or spinning solutions are modified with additives to achieve special fiber properties, the pH of the mash can be lower than 11 - 12. If the molding or spinning solution is used with weakly acidic ion exchangers, e.g. Acrylic acid-divinylbenzene copolymer with bonded carboxylic acid groups, applied to the production of ion exchange fibers, the pH is 9-10. Similar conditions exist in the production of fibers which have an increased water retention capacity, achieved by the Incorpo-. ration of weakly cross-linked polyacrylic acid, which is approximately _-_ 60% neutralized with sodium hydroxide solution, referred to as super absorber.
  • weakly acidic ion exchangers e.g. Acrylic acid-divinylbenzene copolymer with bonded carboxylic acid groups
  • Modifying the form or spinning solution with activated carbon also leads to an increased formation of acid Ren, which lower the pH value and can therefore lead to severe instability of the molding or spinning solution.
  • the stabilizers of the invention correspondingly reduce the breakdown of the cellulose when dissolved in NMMO and during processing, in particular when using additives such as.
  • the dynamic viscosity (zero shear viscosity) was measured with the "Rheostress 100" rheometer with the TC 500 temperature control device from Haake (reference temperature 85 ° C.). The measurements were carried out immediately after the molding or spinning solution had been prepared.
  • the temperature and pressure curve were followed using two measuring methods:
  • the UV / VIS spectroscopy method was chosen to assess the kinetic changes in the form or spinning solutions.
  • the changes in absorption spectroscopy were investigated as a function of temperature in the wavelength range from 200 to 600 nm and as a function of time at a constant wavelength of 400 nm.
  • a temperature-controlled cuvette was constructed which met the special requirements of such samples and which was then inserted into a spectrometer from Shimadzu of the UV-2401 PC type.
  • the thermostability tests were carried out using a PID controller (varistor type K, ⁇ T 0.1 K) with a heating power of the cuvette of 50 W and an optical layer thickness of 350 ⁇ m.
  • the isothermal temperature control from ambient temperature to 150 ° C was freely selectable for absorption spectra and time curves.
  • the most suitable comparison temperature for the molding or spinning solutions was 120 ° C.
  • the color changes occurring in the form or spinning solutions were determined from an eluate with water, which corresponded to a ratio of 1: 3. 10 g of the comminuted form or spinning solution were mixed with 30 ml of distilled water at ambient temperature and the eluate obtained was measured after 48 h at a wavelength of 470 nm in absorbance to determine the E (470) value.
  • the formaldehyde was determined after the preparation of the molding or spinning solution. 5 ml of aqueous eluate (see UV / VIS method) were mixed with 4 ml of acetonitrile and 0.5 ml of 2,4-dinitrophenylhydrazine solution and made up to 10 ml with distilled water. The solution is measured after one hour using HPLC with a diode array detector UV 340 (DIONEX).
  • Table 1 shows the stabilizing effect of the stabilizers according to the invention using the example of a weakly acidic ion exchanger.
  • the molding or spinning solutions listed in Table 1 were prepared in a laboratory kneader. Method :
  • NMMO N-methylmorpholine-N-oxide
  • DP degree of polymerization
  • the test methods described such as the dynamic viscosity, tests in the mini autoclave and the UV / VIS method were used.
  • the aqueous eluates were measured by absorption spectroscopy at a wavelength of 470 nm. sen.
  • the amount of formaldehyde formed and the pH in the aqueous eluate of the spinning solution were assessed as a further stability criterion.
  • Solution 2 was prepared as in Example 1.
  • Solution 3 was prepared analogously to Example 1.
  • SDB styrene-divinylbenzene copolymer with chelating iminodiacetic acid sodium salt
  • SDB styrene-divinylbenzene copolymer-bound benzylamine
  • a direct measurement of the DP of the cellulose is not possible with solid particles in the molding or spinning solution.
  • the viscosity of the form or spinning solution must therefore be used as a measure for evaluating the DP breakdown of the cellulose.
  • a comparison of the viscosities after the preparation of the spinning solution shows that the stabilizers according to the invention according to Example 3 best stabilize the breakdown of the cellulose.
  • the pressure rise is lowest in the mini autoclave and only reaches its maximum after 10 hours.
  • the onset temperature also reaches its highest value at 156 ° C.
  • Table 2 shows the test according to the UV / VIS method.
  • the spinning solutions according to Examples 1 and 2 already show an exothermic reaction after less than 100 minutes, while the spinning solution according to Example 3 runs through after 400 minutes until the measurement is stopped.
  • Figure 1 shows the course of the measurement curves.
  • Example 3 the measurement of the eluate shows less chromophore formation.
  • the formaldehyde formation is at of the spinning solution 3 is significantly lower than that of the spinning solutions according to Examples 1 and 2.
  • Example 4 To prepare the molding or spinning solution, 196 g of NMMO (49.6%) and 13.73 g of spruce pulp with a residual moisture content of 7.5% by mass and a DP of approx. 495 were added to the reactor and according to Example 1 solved. At the end of the solution preparation, 6.59 g of superabsorbent were suspended in 19.3 g of NMMO (80.2%) and added to the spinning solution.
  • Solution 5 was prepared analogously to Example 4. For stabilization, 0.06 mass% of propyl gallic acid and 0.04 mass% of sodium hydroxide solution, based on the spinning solution, were added.
  • Solution 6 was prepared analogously to Example 4. The stabilization was carried out analogously to Example 3.
  • Solution 7 was prepared analogously to Example 4. For stabilization, 0.04 mass% sodium hydroxide solution, 0.03 mass% propyl gallic acid and 0.1 mass% styrene-divinylbenzene copolymer with chelating iododiacetic acid sodium salt (SDI) and 0.10 mass% hydroxylamine added.
  • SDI chelating iododiacetic acid sodium salt
  • the introduced superabsorbent based on polyacrylate has, in a comparable way, destabilizing COOH groups. It can also be seen here that the cellulose and NMMO breakdown are lowest with the stabilization according to the invention (Examples 6 and 7). The thermal stability achieved is significantly better. The course of the curves is shown in FIG. With the unstabilized spinning solution, an exotherm appears after approx. 300 minutes. In the spinning solution stabilized with propyl gallic acid and sodium hydroxide solution, inhomogeneities in the spinning solution occur after 180 minutes, which lead to the measurement being terminated. The spinning solutions stabilizing according to the invention show good thermal stability.
  • Solution 8 was also prepared analogously to Example 1. 227.3 g of 49.6% NMMO were placed in a laboratory reactor and 13.9 g of spruce pulp with a residual moisture of 7.5% by mass and a DP of approx. 495 and 6.45 g of weakly reactive activated carbon were weighed out.
  • Solution 9 was prepared analogously to Example 8. For stabilization, 0.06 mass% of propyl gallic acid and 0.04 mass% of sodium hydroxide solution, based on the spinning solution, were added.
  • Example 10 Solution 10 was prepared according to Example 8. The stabilization was carried out according to Example 3 with 0.21% by weight of styrene-divinylbenzene copolymer with chelating sodium salt of SD (SDI) and 0.21% by weight of styrene-divinylbenzene copolymer-bound benzylamine (SDB).
  • SDI chelating sodium salt of SD
  • SDB styrene-divinylbenzene copolymer-bound benzylamine
  • Solution 11 was prepared as in Example 8.
  • 0.06 mass% propyl gallic acid, 0.04 mass% sodium hydroxide solution and 0.21 mass% styrene-divinyl copolymer-bound benzylamine (SDB) were used.
  • Examples 10 and 11 achieve the highest viscosity of the spinning solution and a significant reduction in the formation of formaldehyde.
  • the reduction in formaldehyde formation is an expression of a lower decomposition of the NMMO.
  • the pressure increases over time shown in FIG. 3 are significantly lower in Examples 10 and 11, which is an expression of an improved thermal stability of the spinning solutions.

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Artificial Filaments (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne un procédé pour produire des solutions à mouler ou à filer thermostables qui contiennent de la cellulose, un aminoxyde tertiaire stable aqueux, de préférence du N-méthylmorpholine-N-oxyde (NMMO), un non-solvant de cellulose, notamment de l'eau, des stabilisants et des additifs permettant de modifier des caractéristiques. Ces solutions sont filées d'après le processus d'extrusion sèche et humide en fibres cellulosiques ou sont laminées en films. Cette invention est caractérisée en ce que la solution contient au moins 0,01 % en poids, par rapport à la solution de filage, d'un ou plusieurs stabilisants qui contiennent des groupes liés à des polymères permettant une liaison d'ion métallique et/ou une liaison d'aldéhyde dans une solution de filage suffisamment basique.
PCT/DE2004/001235 2003-07-11 2004-06-09 Matiere a mouler ou a filer thermostable WO2005007946A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AT0923604A AT504005B1 (de) 2003-07-11 2004-06-09 Thermostabile form- oder spinnmasse
GB0600707A GB2419885C (en) 2003-07-11 2004-06-09 Thermostable molding or spinning compound

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10331342A DE10331342B4 (de) 2003-07-11 2003-07-11 Thermostabile Form- oder Spinnmasse
DE10331342.7 2003-07-11

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Cited By (7)

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EP1698717A1 (fr) * 2005-03-04 2006-09-06 Thüringisches Institut Für Textil- Und Kunststoff-Forschung E.V. stabilisation thermique de solution filöes de lyocell
WO2008009273A1 (fr) * 2006-07-18 2008-01-24 Thüringisches Institut Für Textil- Und Kunstsstoff-Forschung E.V. Procédé de stabilisation de la solution de filage lors de la fabrication de corps moulés composites cellulosiques
WO2009021259A2 (fr) 2007-08-16 2009-02-19 Helfenberger Immobilien Llc & Co Textilforschungs- Und Entwicklungs Keg Mélange, en particulier solution de filage
WO2011100777A1 (fr) * 2010-02-18 2011-08-25 Helfenberger Immobilien Llc & Co Textilforschungs- Und Entwicklungs Kg Mélange et procédé de fabrication d'une fibre
CN103590125B (zh) * 2013-11-11 2016-01-13 江苏宝润科技有限公司 一种具有多功能的复合lyocell纤维及其制备方法
CN106087088A (zh) * 2016-06-15 2016-11-09 唐山三友集团兴达化纤有限公司 再生纤维素纤维的制备方法
AU2017200352B2 (en) * 2010-06-01 2018-08-02 Auspex Pharmaceuticals, Inc. Benzoquinolone inhibitors of VMAT2

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CZ302504B6 (cs) 2009-12-11 2011-06-22 Contipro C A.S. Derivát kyseliny hyaluronové oxidovaný v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd, zpusob jeho prípravy a zpusob jeho modifikace
CZ2009835A3 (cs) 2009-12-11 2011-06-22 Contipro C A.S. Zpusob prípravy derivátu kyseliny hyaluronové oxidovaného v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd a zpusob jeho modifikace
EP2657305B1 (fr) * 2010-12-24 2019-01-23 DIC Corporation Encre à base d'eau pour impression par jet d'encre et procédé de fabrication de l'encre à base d'eau
CZ302994B6 (cs) 2010-12-31 2012-02-08 Cpn S.R.O. Hyaluronová vlákna, zpusob jejich prípravy a použití
CZ303879B6 (cs) 2012-02-28 2013-06-05 Contipro Biotech S.R.O. Deriváty na bázi kyseliny hyaluronové schopné tvorit hydrogely, zpusob jejich prípravy, hydrogely na bázi techto derivátu, zpusob jejich prípravy a pouzití
CZ304651B6 (cs) 2012-05-11 2014-08-20 Contipro Biotech S.R.O. Způsob přípravy mikrovláken, způsob výroby krytů ran, kryty ran a zařízení pro přípravu polysacharidových vláken
CZ304512B6 (cs) 2012-08-08 2014-06-11 Contipro Biotech S.R.O. Derivát kyseliny hyaluronové, způsob jeho přípravy, způsob jeho modifikace a použití
CZ304654B6 (cs) 2012-11-27 2014-08-20 Contipro Biotech S.R.O. Nanomicelární kompozice na bázi C6-C18-acylovaného hyaluronanu, způsob přípravy C6-C18-acylovaného hyaluronanu, způsob přípravy nanomicelární kompozice a stabilizované nanomicelární kompozice a použití
CZ305153B6 (cs) 2014-03-11 2015-05-20 Contipro Biotech S.R.O. Konjugáty oligomeru kyseliny hyaluronové nebo její soli, způsob jejich přípravy a použití
CZ2014451A3 (cs) 2014-06-30 2016-01-13 Contipro Pharma A.S. Protinádorová kompozice na bázi kyseliny hyaluronové a anorganických nanočástic, způsob její přípravy a použití
CZ309295B6 (cs) 2015-03-09 2022-08-10 Contipro A.S. Samonosný, biodegradabilní film na bázi hydrofobizované kyseliny hyaluronové, způsob jeho přípravy a použití
CZ2015398A3 (cs) 2015-06-15 2017-02-08 Contipro A.S. Způsob síťování polysacharidů s využitím fotolabilních chránicích skupin
CZ306662B6 (cs) 2015-06-26 2017-04-26 Contipro A.S. Deriváty sulfatovaných polysacharidů, způsob jejich přípravy, způsob jejich modifikace a použití
CN105525376B (zh) * 2015-11-27 2018-03-27 济南圣泉集团股份有限公司 一种再生纤维素纤维及其制备方法
CZ308106B6 (cs) 2016-06-27 2020-01-08 Contipro A.S. Nenasycené deriváty polysacharidů, způsob jejich přípravy a jejich použití

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DE3034685A1 (de) * 1980-09-13 1982-04-08 Akzo Gmbh, 5600 Wuppertal Cellulose- form- und spinnmasse mit geringen anteilen an niedermolekularen abbauprodukten
DD218104A1 (de) * 1983-10-17 1985-01-30 Veb Chemie Komb. Schwarza "Wilhelm Pieck",Dd Verfahren zur herstellung thermisch stabiler cellulose-aminoxid-loesungen
DD254199A1 (de) * 1986-12-04 1988-02-17 Schwarza Chemiefaser Verfahren zur reinigung waessriger n-methylmorpholin-n-oxyd-loesungen
WO2000063470A1 (fr) * 1999-04-19 2000-10-26 Thüringisches Institut für Textil- und Kunststoff-Forschung e.V. Procede de production de corps moules cellulosiques a haute capacite d'adsorption
WO2003012182A1 (fr) * 2001-07-31 2003-02-13 Stockhausen Gmbh & Co. Kg Procede pour produire des corps façonnes cellulosiques superabsorbants

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1698717A1 (fr) * 2005-03-04 2006-09-06 Thüringisches Institut Für Textil- Und Kunststoff-Forschung E.V. stabilisation thermique de solution filöes de lyocell
WO2008009273A1 (fr) * 2006-07-18 2008-01-24 Thüringisches Institut Für Textil- Und Kunstsstoff-Forschung E.V. Procédé de stabilisation de la solution de filage lors de la fabrication de corps moulés composites cellulosiques
WO2009021259A2 (fr) 2007-08-16 2009-02-19 Helfenberger Immobilien Llc & Co Textilforschungs- Und Entwicklungs Keg Mélange, en particulier solution de filage
WO2009021259A3 (fr) * 2007-08-16 2009-09-11 Helfenberger Immobilien Llc & Co Textilforschungs- Und Entwicklungs Keg Mélange, en particulier solution de filage
US8709272B2 (en) 2007-08-16 2014-04-29 Helfenberger Immobilien Llc & Co Textilforschungs- Und Entwicklungs Keg Mixture, especially spinning solution
WO2011100777A1 (fr) * 2010-02-18 2011-08-25 Helfenberger Immobilien Llc & Co Textilforschungs- Und Entwicklungs Kg Mélange et procédé de fabrication d'une fibre
US9415372B2 (en) 2010-02-18 2016-08-16 Helfenberger Immobilien Llc & Co Textilforschungs—Und Entwicklungs Kg Method for producing a fiber
AU2017200352B2 (en) * 2010-06-01 2018-08-02 Auspex Pharmaceuticals, Inc. Benzoquinolone inhibitors of VMAT2
CN103590125B (zh) * 2013-11-11 2016-01-13 江苏宝润科技有限公司 一种具有多功能的复合lyocell纤维及其制备方法
CN106087088A (zh) * 2016-06-15 2016-11-09 唐山三友集团兴达化纤有限公司 再生纤维素纤维的制备方法

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GB2419885C (en) 2008-04-02
AT504005B1 (de) 2008-03-15
DE10331342A1 (de) 2005-02-10
DE10331342B4 (de) 2009-03-12
GB0600707D0 (en) 2006-02-22
GB2419885B (en) 2007-12-27
GB2419885A (en) 2006-05-10

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